SU197050A1 - METHOD OF OBTAINING DYES - DERIVATIVES OF 1-AMINOANTHRAIN-2-CARBONIC ACIDS - Google Patents

Description

This invention relates to the field of producing dyes suitable for dacron coloring. Dyes give a very bright color with good properties to light, wet treatments and sublimation.

The proposed method consists in the interaction of 1-aminoanthraquinone-2-carboxylic acid chlorides containing in the 4th position various substituents, for example methyl, OXI-, halides, with phenols (phenols).

Example 1. 4.0 g (0.015 mol) of 1-aminoanthraquinone-2-carboxylic acid, 2.15 ml (0.030 mol of thionyl chloride and 50 ml of benzene are boiled for 2 hours. The reaction mixture is cooled, and α-amino-anthraquinone-2-carboxylic acid precipitates acid, which is filtered off and dried under vacuum. Yield 3.5 g (81.6%).

2.00 g (0.007 mol) of 1-aminoanthraquinone-2-carboxylic acid chloride are added to a mixture of 0.78 g (0.0084 mol) of phenol, 0.34 g (0.0084 mol) of caustic soda and 8 ml of acetone and stir at room temperature for 1 hour. The resulting suspension is filtered, the precipitate is washed with 3% soda solution until no colored drops of the filtrate, then with water and dried at 80 ° C. Yield 2.0 g (80%). Get red crystals from butanol, so pl. 197-188 ° C (corr.).

The product colors lavsan in bright orange color with high durability to light and sublimation.

Example 2. Analogously to example 1, from 5.2 g of 1-amino-4-bromoanthraquinone-2-carboxylic acid, 4.38 g (yield 80%) of 1-amio-4-bromo-anthraquinone-2-carboxylic acid chloride are obtained. 2.69 g (0.0055 moles) of 1-amino-4-bromoanthraquinone-2-carboxylic acid chloroaphy Drida is added to a mixture of 1.68 g (0.01878 mol) of phenol, 0.72 g (0.01778 mol) sodium hydroxide and 15 ml of water and stirred at room temperature for 1 hour. The suspension is filtered, the precipitate is shed with 3% sul1 soda solution until no colored filtrate droplets, then water (from soda) and dried at 80 ° C. Yield 1.70 g (65%). Get red crystals from butaiola, so pl. 124-126 ° C (corr.). The product paints lavsan in scarlet color with good strength to wet treatments and sublimation.

Example 3. Analog to Example 1 of 4.4 g of 1-amino-4-oxyangraquinone-2-carboxylic KIS.1OTA, 4.25 g (yield 85%) of 1-amino-4-oxyanthraquinone-2-carbonoBoic acid chloride are obtained. 2.19 f (0.007 mol of acid chloride 1 -a I1PO-4-oxyanthrathion-2-carboxylic acid is introduced into a mixture of 1.78 g (0.01878 mol) of phenol, 0.70 g (0.0178 mol) of sodium hydroxide and 20 ml of water and stir

at room temperature for 1 hour. The suspension obtained is filtered, the precipitate is washed with a 3% soda solution in water until it is free of colored filtrate droplets, then with water (from soda) dried at. Yield 1.53 g (70%). Get purple crystals from butanol, so pl. 142.5-244.5 ° C. The product paints lavsan in purple with good strength to sublimapia and wet treatments.

Example 4. 6.78 g (0.024 mol) of 1-aminoanthrachipon-2-carbopic acid chloride was added to a mixture of 4.17 g (0.048 mol of p-chlorophenol, 1.9 g (0.048 mol of caustic soda and 50 ml of acetone) and stirred at room temperature in tehepep 1 hour. The suspension is filtered, the precipitate is washed with 3% soda solution (until no colored drops), then with water (from soda) and dried at. Yield 4.66 g (66%) / i- 1-amipoanthraquinone-2-carboxylic acid chlorophenyl ester. Orange crystals are obtained from butanol, mp 244.5-245 ° С (corr.). The product colors lavsap in scarlet -y.

Example 5. 2 g (0.00675 mol 1-amino-4 methylaminoanthraquinone-2-carboxylic acid, 3.54 g (0.01770 mol phosphorus pentachloride)

and 20 ml of dry chlorobenzene is stirred for 2 hours at a temperature of 1 hour. The reaction mass is filtered, washed with 20 ml of chlorobenzene, dried under vacuum. The yield of 1.8 g (85%). 1.8 g (0.057 mol of 1-amino-4-methylaminoanthraquinone-2-carboxylic acid chlorohydride) are introduced into a mixture of 1.9 g (0.0202 mol) of phenol and 0.81 g (0.0105 mol of caustic soda and 5 ml water and stirred for 3 hours at room temperature. The resulting suspension is filtered, washed with 3% bicarbonate solution until colorless drops, then with water and dried. -

223 ° С (correspondent). The product colors lavsan in blue-green color.

Prevention and Consideration

A method for producing dyes derived from 1-amipoanthraquinone-2-carboxylic acids, characterized in that, in order to expand the assortment of aprachinone dyes for lassan, 1-aminoanthraquinop2-carboxylic acid chlorides containing, in the 4th position, various substitutes, such as methane. l-, oxy-, halides, are reacted with phenols (phenols).